- Cyclic alpha-dehydroamino ketones, chiral cyclic alpha-amino ketone and preparation method thereof
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The invention provides cyclic alpha-dehydroamino ketones, chiral cyclic alpha-amino ketone and a preparation method of the chiral cyclic alpha-amino ketone. The preparation method comprises the following steps: enabling the cyclic alpha-dehydroamino ketones as shown in a general formula (1) to react in an organic solvent at a hydrogen atmosphere under the catalytic effect of diphosphine-rhodium complex to obtain the chiral cyclic alpha-amino ketone as shown in a general formula (2). The preparation method adopts an asymmetric catalytic hydrogenation, is simple and effective in process, and is suitable for industrial large-scale production. The product, chiral amino ketone, prepared according to the method can be further derived into chiral amino ketone alcohol ligand and chiral amino medicine intermediate, thus having wide application in the industry.
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- Practical Synthetic Procedures for the Iron-Catalyzed Intermolecular Olefin Aminohydroxylation Using Functionalized Hydroxylamines
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A set of practical synthetic procedures for the iron-catalyzed intermolecular olefin aminohydroxylation reactions in gram scale is reported. In these transformations, a bench-stable functionalized hydroxylamine is applied as the amination reagent. This method is compatible with a broad range of synthetically valuable olefins including those that are incompatible with the existing aminohydroxylation methods. It also provides valuable amino alcohol building blocks with regio- and stereochemical arrays that are complementary to known methods.
- Zhu, Cheng-Liang,Lu, Deng-Fu,Sears, Jeffrey D.,Jia, Zhen-Xin,Xu, Hao
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supporting information
p. 3031 - 3041
(2016/09/09)
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- Cyclic trans-β-amino alcohols: Preparation and enzymatic kinetic resolution
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Enantioenriched cyclic β-amino alcohols, trans-2-aminocyclohexanols (ee, >99%), trans-2-aminocyclopentanols (ee, >99%), trans-1-amino-2- indanols (ee, >99%) and trans-2-amino-1-indanols (ee, ～98%) were prepared in high yields via an Arthrobacter sp. Lipase/PLAP catalyzed kinetic resolution of racemic phthalimido acetates. The addition of toluene as a co-solvent dramatically improved the hydrolysis and enantioselectivity, whereas for indanols, substrate immobilization on Celite improved the efficacy of the kinetic resolution.
- Rouf, Abdul,Gupta, Pankaj,Aga, Mushtaq A.,Kumar, Brijesh,Parshad, Rajinder,Taneja, Subhash C.
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p. 2134 - 2143
(2012/05/04)
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- PREPARATION OF IMIDAZOLE DERIVATIVES AND METHODS OF USE
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This invention relates to imidazole compounds which are useful in promoting smoking cessation and maintaining abstinence.
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Page/Page column 50-51
(2010/02/14)
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- Efficient synthesis of a chiral mediator
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An efficient method for the quantitative preparation and isolation of a compound of formula I STR1 or its enantiomer, a chiral mediator used in enantioselective synthesis.
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- Stereoselective synthesis of 1,2-amino alcohols by asymmetric borane reduction of α-oxoketoxime ethers
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Asymmetric reduction of α-oxoketoxime ethers with the reagents prepared in situ from trimethyl borate and chiral amino alcohols derived from either L-proline or α-pinene was investigated. Both cyclic and acyclic α- oxoketoxime ethers were reduced to afford the corresponding chiral 1,2amino alcohols with high enantioselectivities.
- Masui, Moriyasu,Shioiri, Takayuki
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p. 5195 - 5198
(2007/10/03)
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- Enzymatic hydroxylation by dopamine β-hydroxylase
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The three-dimensional aspects of the chemistry of dopamine β-hydroxylase (DBH) was studied through a conformationally-restricted substrate analog approach. We found that the DBH-catalyzed hydroxylation of 2-aminoindane (1) exclusively produced the trans-(1S,2S)-2-amino-1-indanol (4S) (93% ee) in contrast to the stereochemical course of the pro-R hydroxylation of the DBH/phenethylamine reaction. Studies with stereospecifically deuterium labeled 2-aminoindanes 2 and 3 show that the production of (1S)-aminoindanol 4S is the result of stereospecific pro-S hydrogen abstraction followed by the oxygen binding with overall retention of configuration. On the basis of these findings, we propose a model for the interaction of the phenethylamine substrates with the enzyme.
- Mitrochkine, Anton A.,Eydoux, Frank,Gil, Gerard,Reglier, Marius
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p. 1171 - 1176
(2007/10/03)
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- Synthesis of Enantiomerically Pure cis and trans-2-Amino-1-indanol
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Enantiomerically pure cis and trans-2-amino-1-indanols 1 and 2 were synthesized via a highly enetioslective lipase catalyzed transestrification of racemic cis-2-azido-1-indanol 3.
- Mitrochkine, Anton,Gil, Gerard,Reglier, Marius
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p. 1535 - 1538
(2007/10/02)
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- CATALYTIC ENANTIOSELECTIVE DIELS-ALDER REACTIONS USING TITANIUM COMPLEXES OF CIS-N-SULFONYL-2-AMINO-1-INDANOLS
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A titanium complex derived from (1R,2S)-N-(2,4,6-trimethylbenzenesulfonyl)-2-amino-1-indanol catalyzes the Diels-Alder reaction of 2-bromoacrolein and cyclopentadiene with 96.5:3.5 enantioselectivity.A new and efficient synthesis of 2-amino-1-indanol (6)
- Corey, E. J.,Roper, Thomas D.,Ishihara, Kazuaki,Sarakinos, Georgios
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p. 8399 - 8402
(2007/10/02)
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- COPPER(II) IN ORGANIC SYNTHESIS. X. THE IMPORTANCE OF STERIC HINDRANCE IN THE DESIGN OF CHIRAL TRIDENTATE LIGAND COPPER(II) CATALYSTS FOR ENANTIOSELECTIVE MICHAEL REACTIONS
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Several copper(II) complexes with tridentate chiral ligands derived from 2-substituted 2-aminoethanols have been tested as catalysts for enantioselective Michael reactions.The degree of enantioselection increases with the increase of the steric hindrance of the substituents and the best result (65percent e.e.) was obtained with the benzyl-substituted catalyst.A comparison of these results with those obtained with complexes derived from 2-amino-1-indanols gives useful information about the requirements for the optimization of the catalyst design.
- Desimoni, Giovanni,Faita, Giuseppe,Mellerio, Giorgio,Righetti, Pier Paolo,Zanelli, Claudio
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p. 269 - 273
(2007/10/02)
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